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The Caribbean charter season runs December through mid-April. Three windows carry a peak premium: the Christmas week, the New Year week (which is the highest-priced charter week on earth, ahead of even Cannes during the Film Festival), and the U.S. Presidents' Week in mid-February. A 50m motor yacht out of Saint Thomas that runs $310,000 a week in the second week of January will run $480,000 over New Year and $260,000 in late March, for the same yacht, the same crew, and a coastline that is calmer in the back half of the season.
Roughly 400 charter yachts work the Caribbean season at 30m and above. The fleet is smaller than the Med (about a third of the size by volume) but more concentrated around the three or four primary cruising grounds. Most Caribbean charters operate in the same 200 nautical mile band stretching from the Virgin Islands down through the Leewards. The BVI alone handles about 40 percent of weekly Caribbean charter bookings.
We cover 11 Caribbean charter destinations, organized by where the yacht actually anchors, not by which island it cleared customs at. The difference matters. A "Saint-Barths" charter is usually four nights in Saint-Barths and three nights in the Saint Martin lagoon, because the Saint-Barths anchorages do not absorb the fleet of yachts that show up for New Year.
When to go
The Caribbean season has four distinct windows.
Mid-November to mid-December. Yachts arrive from the Mediterranean repositioning. Crews settle into Caribbean rotation. The Atlantic hurricane season officially ends November 30 and inventory opens up. Prices are at or near low-season rates. Water is at 27 degrees Celsius. The downside is that yachts arriving from refit or Atlantic crossings sometimes need a settling week, and the fleet is at its smallest. We have seen captains report the boat as ready and surface mechanical issues mid-charter in this window more often than later in the season. Brokers know this. The good ones will not book first-trip clients in the first two weeks of December.
Christmas, New Year, and the week between. Three of the four most expensive charter weeks on earth. New Year specifically is impossible to book inside twelve months for any yacht above 40m. Premium over baseline is roughly 35 to 50 percent on rate. The Virgin Islands, Saint-Barths, and Saint Martin are at full crowd. Most of the high-end yachts are in Saint-Barths or anchored off Anguilla.
Mid-January through mid-March. The core Caribbean season. Stable weather, full fleet, the broadest yacht selection, and the rates between the peak weeks are 15 to 25 percent below the holiday weeks. Presidents' Week in February is a single-week premium. Most of the strongest charter weeks of the year for first-time Caribbean clients fall here.
Late March through April. Water is at its warmest, around 28 degrees. Trade winds soften. Prices fall from late March. April first three weeks are the best value of the Caribbean season for a client who can travel outside school holidays. Most yachts begin repositioning to the Mediterranean from late April.
Where to go
The 11 destinations fall into four clusters.
The Virgin Islands and adjacent. BVI is the first-time charter destination on earth. Short hops, sheltered anchorages, the easiest sailing chartering in the world. Anchorage protection is unmatched in the Caribbean. The cluster includes Norman Island, Peter Island, Cooper, Salt Island, Virgin Gorda, the Baths, Anegada, and Jost Van Dyke. The US Virgin Islands (St. Thomas, St. John) sit on the same cluster but with different customs and a smaller charter fleet.
The northern Leewards. Saint-Barths is the highest-premium destination in the region. Gustavia harbor, Colombier, Saline Bay, and the Anse de Grand Cul-de-Sac are the anchorage rotation. Saint Martin and Anguilla flank Saint-Barths and serve as overflow anchorages and provisioning bases. Most New Year and Saint-Barths charters move between the three.
The Bahamas and northern Caribbean. Bahamas is a separate market with Bahamian-flag complications, glass water, and harder provisioning than the Caribbean proper. The Exumas are the headline cluster (Staniel Cay, Compass Cay, Highbourne) and the Abacos are the quieter northern alternative.
The southern Leewards and Windwards. Antigua, Saint Lucia, and the Grenadines are the longer-passage Caribbean. Real sailing routes, anchorage spacing of 30 to 80 nautical miles, and the highest-quality sailing-yacht charter inventory in the region. Antigua is the dispatch hub, with English Harbour and Falmouth Harbour as the dock anchors.
How Caribbean charter cost actually works
The Caribbean has a slightly different cost structure from the Med. No VAT, but the APA conventions are higher, fuel is more expensive on outer islands, and the gratuity norm is one to two points higher.
| Line item | Typical range | Notes |
|---|---|---|
| Weekly rate | $50K to $1.5M+ | 24m catamaran at the low end, 100m motor yacht at the high end |
| APA | 28-35% of weekly rate | Higher than Mediterranean. Fuel and provisioning in outer islands. |
| VAT | 0% | The major cost advantage versus the Med. |
| Gratuity | 10-12% of weekly rate | 12% is the Caribbean motor-yacht norm. 10% on sailing. |
| Total full check | 1.4-1.5x headline | $300K headline lands at $420K-$450K for the trip. |
The Caribbean weekly rates and yacht crew gratuity by region guides have full tables.
The math difference versus the Med is meaningful. A $400K headline week in the Med (1.5x ratio) and a $400K headline week in the Caribbean (1.45x ratio) produce a $20K to $30K difference in total check, in favor of the Caribbean. For a comparable yacht, the Caribbean is usually 5 to 10 percent cheaper all-in than the Med, with the exception of the New Year peak.
Trip shape: what each cluster is for
A common decision is BVI versus Bahamas versus Saint-Barths. The right answer depends on what the trip is meant to be.
The BVI is for clients who want short days at sea, anchored time, watersports, and minimal dependence on what is happening ashore. Most nights are aboard, with one or two dinners ashore in places like Pirate's Bight, Cooper Island, or Saba Rock. The anchorages are sheltered enough that sleep quality is consistently good. This is the right answer for first-time charter, families, and groups with mixed sea experience.
The Bahamas is for clients who want the cleanest water on the planet, with the trip organized around swimming and tender expeditions to Pig Beach, Thunderball Grotto, the swimming pigs, and the various sand bars. The Exumas anchorages are exposed when the cold fronts come through in January and February, and Bahamian customs is the slowest in the region. Provisioning is genuinely harder than Caribbean proper. Worth it if you have done the BVI before.
Saint-Barths and the northern Leewards are for clients who want the trip to include the scene. The yacht is the venue but the ports ashore (Gustavia, Saint Martin, Anguilla beaches) are an active part of the agenda. The New Year crowd is exactly that. The rest of the season is calmer and the yacht selection is still strong.
The southern Leewards and Grenadines are for sailing clients on yachts in the 40m to 70m range who want real passage-making between anchorages. Antigua to Saint Lucia is a 230 nautical mile run, broken into legs at Guadeloupe and Dominica. This is the closest the modern Caribbean charter market gets to actual blue-water sailing on a charter calendar. The motor-yacht crowd does not usually book this corridor.
What we passed on
Three Caribbean clusters are deliberately not on the 2026 index.
The southern Caribbean (Aruba, Bonaire, Curaçao, the ABC Islands) has the geography for great yacht weeks but the charter inventory is light and the windward passage from the eastern Caribbean is rougher than most charter clients book. Better suited as a destination from a yacht-owned base than as a chartered week.
Cuba is operationally complex for U.S.-flagged or U.S.-passport charter clients and the charter infrastructure for non-U.S. clients is inconsistent. Until that picture stabilizes we will not publish a destination guide that recommends a charter there with confidence.
The Cayman Islands are not a charter destination in the meaningful sense. The Caymans serve as a yacht-management and flag-state hub. They are not where charter clients usually plan a week.
Sailing versus motor in the Caribbean
The Caribbean has the strongest sailing-yacht charter inventory on earth. The trade winds are stable. The anchorages are spaced for sail. The fleet of 30m to 65m sailing yachts based in Antigua, the Grenadines, and the BVI is the deepest on any sea. A Caribbean week on a 40m sailing yacht is genuinely a different trip from a Caribbean week on a 40m motor yacht, and the right answer depends on whether the group wants to feel the boat or feel the destination.
The Med fleet skews heavier toward motor. The Caribbean fleet leans the other way. For most clients who want to charter sail, the Caribbean is the better season to book it.
The rest of the trip
VillasForKings covers the same Caribbean destinations on the villa side, particularly the Caribbean coast of Saint-Barths and the BVI. HotelsForKings covers the Saint-Barths, Anguilla, and Bahamas hotel layovers. RestaurantsForKings and BarsForKings cover what to eat and drink in port.
FAQ
Is the BVI safe after Hurricane Beryl? The 2024 hurricane season caused damage in parts of the eastern Caribbean. The BVI charter infrastructure (marinas, anchorages, restaurants) has largely been re-opened. The Bitter End on Virgin Gorda, partially destroyed in Hurricane Irma in 2017 and only fully re-opened in 2023, is now operating at near-full capacity. Specific anchorage statuses are noted on the BVI destination page.
When does Christmas week pricing kick in? Roughly December 20 through January 2. Some brokers extend the premium one extra week on either side for the most-booked yachts. The premium over baseline is 35 to 50 percent depending on the yacht.
Should I book Saint-Barths for New Year? Only if you have a 14 to 18 month lead time and a budget that absorbs the New Year premium. If you have less than 12 months and you want the Saint-Barths anchorage on New Year, you will not get the yacht you want. The better answer is to anchor off Anguilla or in the Saint Martin lagoon and tender in.
Can I sail one-way from the BVI to Antigua? Yes, with a positioning fee and a longer charter (usually 10 days or two weeks). A handful of yachts will run this as a charter itinerary in March. Most do not.
Do I need to clear customs at every island? Yes. The Caribbean is a customs-heavy charter region. The captain handles the paperwork but you should expect short delays at most island borders. The Grenadines and BVI run multiple jurisdictions within a short distance and the captain's local relationships matter.